关于青霉硫呋醇的合成研究：一种高级螺环二酮哌嗪中间体的合成。
Synthetic studies towards the penicisulfuranols: Synthesis of an advanced spirocyclic diketopiperazine intermediate.
作者信息
Gayler Kevin M, Lambert Kyle M, Wood John L
机构信息
Department of Chemistry and Biochemistry, Baylor University, Waco, TX, 76798, USA.
出版信息
Tetrahedron. 2019 Jun 14;75(24):3154-3159. doi: 10.1016/j.tet.2019.01.032. Epub 2019 Jan 21.
Abstract
The 2,5-diketopiperazine (DKP) moiety is a core feature of many natural products and medicinally relevant scaffolds. As part of our efforts directed towards a total synthesis of penicisulfuranol B, we have developed and report herein: (1) the preparation of an diketopiperazine intermediate accessible via a molybdenum-mediated oxidation of a parent diketopiperazine, and (2) further synthetic studies leading to a novel spirocyclic dihydrobenzofuran-containing diketopiperazine.
摘要
2,5-二酮哌嗪（DKP）部分是许多天然产物和具有药用价值的骨架的核心特征。作为我们全合成青霉硫呋醇B工作的一部分，我们在此开发并报告：（1）通过钼介导的母体二酮哌嗪氧化制备一种二酮哌嗪中间体，以及（2）进一步的合成研究，得到一种含新型螺环二氢苯并呋喃的二酮哌嗪。
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本文引用的文献
1
A Three-Step Entry to the Aspirochlorine Family of Antifungal Agents.
Angew Chem Int Ed Engl. 2000 Nov 3;39(21):3866-3868. doi: 10.1002/1521-3773(20001103)39:21<3866::AID-ANIE3866>3.0.CO;2-E.
2
Penicisulfuranols A-F, Alkaloids from the Mangrove Endophytic Fungus Penicillium janthinellum HDN13-309.
J Nat Prod. 2017 Jan 27;80(1):71-75. doi: 10.1021/acs.jnatprod.6b00483. Epub 2016 Dec 19.
3
Synthesis and activity evaluation of the cyclic dipeptides arylidene N-alkoxydiketopiperazines.
Bioorg Med Chem. 2016 Nov 1;24(21):5197-5205. doi: 10.1016/j.bmc.2016.08.038. Epub 2016 Aug 24.
4
The flavan-isoflavan rearrangement: bioinspired synthetic access to isoflavonoids via 1,2-shift-alkylation sequence.
Chem Commun (Camb). 2015 Apr 25;51(32):7012-4. doi: 10.1039/c5cc01572c. Epub 2015 Mar 24.
5
Novel piperazinediones as antitumor agents.
Anticancer Res. 2014 Aug;34(8):4013-9.
6
Convergent synthesis and structural confirmation of phellodonin and sarcodonin ε.
Org Lett. 2013 May 3;15(9):2080-3. doi: 10.1021/ol400709f. Epub 2013 Apr 11.
7
Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.
J Org Chem. 2011 Feb 18;76(4):1013-30. doi: 10.1021/jo102228j. Epub 2011 Jan 20.
8
Concise and diversity-oriented route toward polysubstituted 2-aminoimidazole alkaloids and their analogues.
Angew Chem Int Ed Engl. 2010 Dec 3;49(49):9465-8. doi: 10.1002/anie.201004256.
9
Structural and biochemical characterization of the cytochrome P450 CypX (CYP134A1) from Bacillus subtilis: a cyclo-L-leucyl-L-leucyl dipeptide oxidase.
Biochemistry. 2010 Aug 31;49(34):7282-96. doi: 10.1021/bi100910y.
10
Hydrogen bonding lowers intrinsic nucleophilicity of solvated nucleophiles.
J Am Chem Soc. 2008 Nov 12;130(45):15038-46. doi: 10.1021/ja802814a. Epub 2008 Oct 18.
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